


500 Days of Castiel Milton

by There_Are_Things_I_Cant_Say



Category: Supernatural
Genre: Alternate Universe, M/M, Romance
Language: English
Status: In-Progress
Published: 2013-01-13
Updated: 2013-01-25
Packaged: 2017-11-25 10:13:01
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 1,640
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/637797
Author URL: https://archiveofourown.org/users/There_Are_Things_I_Cant_Say/pseuds/There_Are_Things_I_Cant_Say
Summary: <blockquote class="userstuff">
              <p>Dean Winchester lives an average life in a job that he doesn't like. But when his boss hires a new assistant, it seems like his luck is going to change for the better. Completely AU Destiel</p>
            </blockquote>





	1. Prologue and Day One

**Author's Note:**

> I watched 500 Days of Summer and I just kept on picturing Dean and Castiel in those roles :') I don't think I've seen a fic like this but if anybody has please tell me because I'd hate to steal anyone's idea or plot. I hope it isn't too bad writing and t probably wont exactly follow the movie story and I apologise if any is ooc :D
> 
> Disclaimer: I own no rights to either Supernatural or 500 Days of Summer, I'm gonna go to my box and cry now

_Prologue ___

__**Day 290 ******__

__****His life was over. It wasn't even an understatement; Dean Winchester was well and truly fucked. It hadn't even been a year and his world had turned upside down, inside out; been broken apart and taped back together just to be split into pieces once again.** ** _ _

__****He closed his eyes and images of dark blue orbs and a mess of untidy black hair invaded his mind everywhere he went. He had known something was off but he hadn't dared himself to think anymore of it. He had never been this happy with somebody, never allowed himself to immerse his heart and soul into one relationship.** ** _ _

__****"I think we should stop seeing each other."** ** _ _

__****Dean looked up from his cheeseburger in shock. Of all the words he had expected to come out of his partner's mouth, never in all of the world was it those eight.** ** _ _

__****Shit.** ** _ _

__******DAY ONE ******** ** _ _

__********"Dude, hurry up!"** ** ** ** _ _

__********Dean called up the stairs to his sixteen year old brother. Sam was a demon in the morning and if he didn't move his ass soon then he would miss first period and Dean was not signing another imaginary dentist slip.** ** ** ** _ _

__********"Alright, alright. Geez."** ** ** ** _ _

__********Sam came clattering down into the kitchen, hopping on one foot in order to pull his sock on properly. He had grown again over the summer Dean noticed as he glanced upwards. Despite the four year age difference Sam towered over his older brother. He chucked the floppy haired teen his satchel and they wandered outside to Dean's prize possession, his impala. Though Sam had his license as well, there was no way the idiot was ever sitting in his baby's driver seat.** ** ** ** _ _

__********"You won't forget about Lisa's engagement party this weekend right?"** ** ** ** _ _

__********Sam asked as they pulled up outside his ridiculously fancy scholarship earned private school. He undid his seat belt and turned to fix Dean with an unnerving stare.** ** ** ** _ _

__********"Right?"** ** ** ** _ _

__********Dean rolled his eyes but was unable to keep the smile off of his face. Sam was an overeager puppy in a vessel; and Dean loved Lisa, he was truly happy that she had found somebody to spend her life with. They weren't a good couple he could see that now, but she was still his best friend, stayed with him while he tried to find himself and always would be there.** ** ** ** _ _

__********"Yeah yeah Sammy, I won't forget I promise. Now scoot, go and learn smart things to put inside of your abnormally large head."** ** ** ** _ _

__********Sam shot Dean the two finger salute as he clambered out of the car with the same gracelessness he applied to the majority of tasks and jogged over to a group of friends that were waiting for him.** ** ** ** _ _

__********Other mother day, seriously?** ** ** ** _ _

__********Dean thought as he tapped his pen against his folder absent minded. The meeting had only been going on for twenty minutes and he was bored out of his mind. He had never wanted to go into the greeting card business but there was no way he could juggle studying for a mechanics degree whilst working here and Ellen's bar in the evening. His main priority was to make sure Sam had everything he needed, that was all that mattered.** ** ** ** _ _

__********"Dude where'd you get to last night?"** ** ** ** _ _

__********Ash, Dean's colleague and sometimes drinking buddy was muttering to him out of the corner of his mouth. He was the graphics designer for the company and had been the one to get the job cemented for Dean.** ** ** ** _ _

__********"Oh yeah sorry Sam needed me to come home."** ** ** ** _ _

__********Ash opened his mouth to reply but was interrupted when the door opened and the newcomer stepped into the conference room. Dean's eyes snapped up to see a man walk over to their boss Crowley and whispered into the Englishman's ear . Crowley straightened up and turned to his employees.** ** ** ** _ _

__********"I'm sorry but there's something I must take care of. Oh uh yes, everybody this is my new assistant Castiel Milton from uh-"** ** ** ** _ _

__********"Massachusetts"** ** ** ** _ _

__********The guy, Castiel, supplied helpfully. Something heavy started to curl in Dean's stomach as the gravely voice reached his ears. Crowley nodded and left the room leaving Castiel standing in front of twenty strangers.** ** ** ** _ _

__********"So uh it was nice to meet you all." The dark haired man tugged on the edge of the ugly trench coat that he was wearing over his suit. He picked up Crowley's empty coffee mug, and made to leave. His gaze swept over the bored faces before eyes landing on Dean. The look was heated and made the hairs on the back of Dean's neck stand on end as if they had been electric shocked.** ** ** ** _ _

__********Damn he was screwed.** ** ** ** _ _


	2. Day One (Cont) and Day Two

_DAY ONE –(Cont) ___

__Dean had managed to avoid human contact with Castiel for most of the day. He had eaten lunch with Ash and the creepy dude Chuck from PR now he was ready to go home and sink into his bed for the night._ _

__Snapping the headphones of his iPod up over his ears, he waved briefly at the few remaining workers and pressed the button of the elevator, tapping his foot in rhythm to the bass guitar in the song. The metal doors opened with a bing and Dean went to step in but stopped when he realised there was a body in the way of the space he had meant to occupy._ _

__Castiel was standing inside of the device, bright blue eyes focused on Dean and his mouth quirked upwards in a small smile. Dean nodded his head in greeting and moved to stand next to the man; fixing his eyes on anywhere but the attractive assistant. Unfortunately the interior was downright ugly and he found himself risking little glances to the side. The third time it happened, he caught Castiel's amused expression and felt a slight blush spreading throughout his face._ _

__"What are you listening to?"_ _

__Castiel enquired slightly louder than necessary so that Dean could hear the question. The elder Winchester lifted the headphone off of the closest ear and shuffled his feet uncomfortably. This damn elevator ride was taking forever._ _

__"Uh, Led Zeppelin"_ _

__At Castiel's blank look, Dean let his jaw drop open in slight surprise._ _

__"Dude, you being serious? Stairway to Heaven, Sick again, Poor Tom?"_ _

__All Dean got in return was a confused head tilt. "I'm sorry Dean but I am not familiar with this music."_ _

__"I- What.. H-How do you know my name is Dean?"_ _

__The elevator grounded to a halt before he could find out how Castiel knew who he was without properly being introduced. Castiel shot him another half smile as he stepped out._ _

__"I have my sources, good night Dean."_ _

__

__"Why are you smiling like that?" Sam's nose wrinkled as he looked up from his homework at his older brother._ _

__Dean turned away from the stove in time to the music playing loudly from the stereo and thrusting the wooden spoon in Sam's direction._ _

__"Taste." He ordered and raised an eyebrow as Sam obediently dabbed a finger in the pasta sauce. "Smiling like what? I'm not smiling like anything."_ _

__"You look like a goof." Sam stated bluntly and grinned all of a sudden as if a light bulb had gone off. "Aw Dean have you met someone?"_ _

__"What? NO!"_ _

__"Oh my God you have!" Sam pushed away his textbook impatiently and leaned across the table, attention intently on his brother. "Who is it? Someone at work I'm guessing. Tell me"_ _

__Dean rolled his eyes at his nosy brother's persistence but couldn't help smiling a little as he met the large hazel orbs doing their best puppy expression._ _

__"Alright fine there might be somebody I'm interested in."_ _

__"Ha I knew it!" Sam pumped a fist in triumph, ignoring the elder Winchester sticking his tongue out childishly at him._ _

__"But I don't even know if he likes dudes let alone if he's available."_ _

__Dean had been hurt too many times that he was definitely on the scale of careful when it came to new people and maintaining even a simple friendship. Sam knew this but all he wanted was that Dean could find a little happiness in his life, God knows he'd been dealt the short straw often enough._ _

___DAY TWO _____

____"So you know that new dude?" Ash was sitting on his desk as Dean came in the next morning. Dean sighed but didn't attempt to move the other man, he knew him too well._ _ _ _

____"Castiel? What about him?"_ _ _ _

____Ash glanced around the office floor before leaning forwards and dropping his voice to a stage whisper._ _ _ _

____"Chuck told me that Meg came onto Castiel yesterday in the copy room and he totally blew her off, he's gotta be batting for our team."_ _ _ _

____Dean rolled his eyes and shoved at Ash's elbow so that he could sit down in his chair. "You shouldn't make assumptions before you know the guy. Maybe he has a sixth sense where he can tell whether or not certain people are crazy bitches from five miles off."_ _ _ _

____"Whatever dude. I mean, yeah each to their own and all that shit but I'd definitely go for it with Meg if I were him."_ _ _ _

____"Well you aren't him." Dean's tone came out colder then he had intended to and he blinked, slightly confused with himself for the sudden streak of defensiveness that had appeared for a man he had only met one day ago._ _ _ _

____Ash hopped effortlessly off of the desk and moved round to his own cubicle opposite of Dean's own one. As Dean sorted out his papers that the other man had messed up, he looked up and noticed that Castiel was watching him from across the room intently. He raised a hand in Castiel's direction and tried not to think about what it meant when his heart flip flopped pathetically at the nod he received in return._ _ _ _

**Author's Note:**

> Commas are my enemy! And I can't do page breaks so sorry D:


End file.
